Hydrochloric Acid → 3,5-Difluoropropiophenone

HRID 1030043Notes

Reaction equation

HRID 1030043 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#N.[CH2:11]([Mg]Br)[CH3:12].Cl.C([O:18]CC)C>>[F:1][C:2]1[CH:3]=[C:4]([C:5](=[O:18])[CH2:11][CH3:12])[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 5872043,5-DifluorobenzonitrileHCID 178418443HCID 178418443, compound

Product 1

HCID 1456203,5-DifluoropropiophenoneYield 91%

Procedure

To a solution of 3,5-difluorobenzonitrile (Aldrich Chemical Co . Milwaukee. WI 53233)(50.0 g. 0.36 mole) in 500 mL of diethyl ether at 0° C. was added dropwise a solution of ethylmagnesium bromide (135 mL of a 3.OM solution 0.41 mole) in diethyl ether. The reaction mixture was refluxed for 3 hr. then chilled in an ice bath and hydrolyzed with 100 mL of 6N aqueous hydrogen chloride. The mixture was heated on a steam bath for 0.5 hr. The pH was adjusted to acid (litmus) and two phases were separated by extraction of the aqueous phase with diethyl ether. The combined extracts were dried (sodium sulfate) and concentrated in vacuo to give 61.3 g (91% of theory) of crude 3',5'-difluoropropiophenone.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hr
  2. temperatureThe mixture was heated on a steam bath for 0.5 hr
  3. customwere separated by extraction of the aqueous phase with diethyl ether
  4. dry with materialThe combined extracts were dried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89c57689e4f24a418bed1c7958fdb9a9
Source dataset
uspto-grants-1992_04
Patent number
US05104870

Reaction notes

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